Benzoquinone derivatives and process of making same.



UNITED STATES PATENT OFFICE.

RUDOLF MAAG, 0F SINDLINGEN, NEAR- HOCHST-ON-THE-MAIN, AND PAUL JORG, OF HOCHST-ON-THE-MAIN, GERMANY, ASSIGNORS TO FARBWERKE VORM. MEISTER LUCIUS & BRUNING, 0F HOCHST-ON-THE-MAIN, GERMANY, A CORPORATION OF GER-MANY.

BENZOQUINONE DERIVATIVES AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

No Drawing. Application filed May 1, 1912, Serial No. 694,542. Renewed March 1, 1913. Serial No. 751,646.

I '0 all whom it may concern Be it known that we, RUDOLF MAAG, Ph. 11, chemist. and PAr'r Jone, Ph. D., chemist, citizens of the Swiss Republic and the German Empire, respectively, residing at Sindlingen. near Hochst-on-the-Main, and Hochst-on-theMain, Germany, respectively, have invented certain new and useful Improvements in Benzoquinone Derivatives and Processes of Making Same, of which the following is a specification.

We have found that by heating the diarylamino derivatives of halogenized benzoquinones corresponding to the constitutional formula:

wherein X stands for a benzene residue which may be substituted, and Y and Z for a halogen, one of which may be replaced by hydrogen, they are transformed into new compounds probably constituting derivatives of the triphendioxazin.

The heating is advantageously effected in a solvent of a high boiling point and in presence of a metal halogenid. \Vhen triturated, they form reddish-brown powders, crystallizing with a bronze luster; they are insoluble in water and alcohol, soluble in concentrated sulfuric acid with a blue color, in boiling Xylene with an intense yellow fluorescence. They are of great value as pigment dyes.

Example: 15 parts of di-(p-phenetipreparing it in a pure state, the product after being dried at 120 C. may be recrystallized in nitrobenzene. It then forms small red needles of a green metallic luster, and when triturated forms a red powder. It is insoluble in water and alcohol, soluble in concentrated sulfuric acid with a blue color, in boiling xylene with a yellow fluorescence. Its composition corresponds most probably to the formula:

W hen made up into a pigment dye, it yields beautiful fast bluish-red tints.

Having now described our invention, what we claim is:

1. The process of manufacturing dyestufis, which consists in heating diarylamino-halogenbenzoquinone derivatives, wherein aryl means a benzene residue which may be substituted, in a solvent of high boiling point.

2. The process of manufacturing dyestuffs, which consists in heatin diarylamino halogen benzoquinone erivatives, wherein aryl means a benzene residue which may be substituted, in a solvent of a high boiling point, in the presence of a metal chlorid.

3. The process of manufacturing a dyestufl', which consists in heating di-paraphenetidino-dichlorbenzoquinone with ferric chlorid in nitr0benzene.--

4. As new products, the dyestuffs being inner condensation-products of di-arvlamino-ha-logen-benzoquinone derivatives, and very probably being derivatives of the triphendioxazin forming red owders, insolu e in water and alcohol, solu le 1n concen rated sulfurlc acid with a blue color and in boiling xylene f and in boiling xylene with an intense yelwith a yellow fluorescence. low fluorescence.

5. As a new product, the dyestufl*' being In testimony wherehf, We afiix our signaan inner condensation-product of di-paratures in presence of two witnesses. 5 phenetidino-dichlorbenzoquinone very robably being a derivative of the triphend ioxa- RUDOLF MAAG' zin, forming a red powder which when PAUL JORG crystallized in nitrobenzene, turns into small Vvitnesses: red needles of a greenish luster, soluble in JEAN GRUND, 10 concentrated sulfuric acid with a blue color CARL GRUND.

Copies of this patent may be obtained for five cents each, by addressing the Commissioner of Patents, Washington, D. C. 

